Hydrochloric Acid → Dimethyl 2-phenyl-3-cyano-6-bromohexane-3,4-dicarboxylate

HRID 325768ノート

反応式

HRID 325768 の反応式
[C:1]([CH:3]([CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:9])[C:4]([O:6][CH3:7])=[O:5])#[N:2].Br[CH:17]([CH2:22][CH2:23][Br:24])[C:18]([O:20][CH3:21])=[O:19].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[C:10]1([CH:8]([C:3]([C:1]#[N:2])([C:4]([O:6][CH3:7])=[O:5])[CH:17]([C:18]([O:20][CH3:21])=[O:19])[CH2:22][CH2:23][Br:24])[CH3:9])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 296716Methyl 2,4-dibromobutanoateHCID 13276234Methyl 2-cyano-3-phenylbutyrate

生成物 1

HCID 13292496Dimethyl 2-phenyl-3-cyano-6-bromohexane-3,4-dicarboxylate

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

A mixture of methyl 2-cyano-3-phenylbutyrate (78 g, 0.37 mole), methyl 2,4-dibromobutyrate (122 g, 0.47 mole), potassium carbonate (65 g, 0.47 mole) and DMSO (50 ml) was stirred on a ball mill apparatus. The reaction was completed in four hours. Ice water was added and the mixture was neutralized by adding cold hydrochloric acid. The aqueous solution was extracted several times with ether. The combined organic solution was washed sequentially with cold aqueous sodium bicarbonate and brine, then dried over magnesium sulfate. After removal of the solvent, the residue was purified by Kugelrohr distillation (100° C., 30 microns) to remove low boiling materials. The remaining oily residue (118 g., 84%) was found to be mainly the title bromide condensation product (μ<95% GC purity). MS m/e (% relative intensity) 383(M.+, 3) 381 (3), 202 (33), 182 (7), 180 (7), 105 (100).

後処理

  1. extractionThe aqueous solution was extracted several times with ether
  2. washThe combined organic solution was washed sequentially with cold aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter removal of the solvent
  5. distillationthe residue was purified by Kugelrohr distillation (100° C., 30 microns)
  6. customto remove low boiling materials
  7. customthe title bromide condensation product (μ<95% GC purity)

出典と根拠

ORDレコード
ord-4b18e8611ba445c49bc054271043bb31
出典データセット
uspto-grants-1984_04
特許番号
US04442298

反応ノート

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